Sodium Cyanide → 2-(4-(Thien-2-ylcarbonyl)phenyl)propiononitrile

HRID 1439574Notes

Reaction equation

HRID 1439574 reaction equation
[C-:1]#[N:2].[Na+].[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH:17](Br)[CH3:18])=[CH:13][CH:12]=1)=[O:10]>CS(C)=O>[C:5]1([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:18])[C:1]#[N:2])=[CH:13][CH:12]=2)=[O:10])[S:4][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 103685[4-(1-Bromoethyl)phenyl](thiophen-2-yl)methanone

Product 1

HCID 1036862-(4-(Thien-2-ylcarbonyl)phenyl)propiononitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 4.9 parts of sodium cyanide in 55 parts of dimethyl sulfoxide is stirred while heating to 60° C. Then there are added at once 10 parts of α-bromo-α-methyl-p-tolyl 2-thienyl ketone and stirring at 60° C is continued for 4h.30. The reaction mixture is poured onto water and the product is extracted with ether. The organic layer is washed with water, dried, filtered and evaporated, yielding p-(2-thenoyl)hydratroponitrile as a residue.

Workup

  1. stirringstirring at 60° C
  2. additionThe reaction mixture is poured onto water
  3. extractionthe product is extracted with ether
  4. washThe organic layer is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1bc129b9b9164923827204ff09b2747d
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Reaction notes

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